Trimethylsilyl iodide → HCID 24856097, compound

HRID 911179Notes

Reaction equation

HRID 911179 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17][C:18]3[CH:55]=[CH:54][C:21]([O:22][C:23]4[C:28]([C:29]5[CH:34]=[CH:33][N:32]=[C:31]([NH:35][P:36](=[O:53])([O:45]CC6C=CC=CC=6)[O:37]CC6C=CC=CC=6)[N:30]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:20][CH:19]=3)=[N:9][N:8]=2)[S:5][CH:6]=1.C(#N)C.C(Cl)Cl.[I:62][Si](C)(C)C>CO>[IH:62].[IH:62].[CH3:1][C:2]1[N:3]=[C:4]([C:7]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([NH:17][C:18]3[CH:55]=[CH:54][C:21]([O:22][C:23]4[C:28]([C:29]5[CH:34]=[CH:33][N:32]=[C:31]([NH:35][P:36](=[O:37])([OH:45])[OH:53])[N:30]=5)=[CH:27][CH:26]=[CH:25][N:24]=4)=[CH:20][CH:19]=3)=[N:9][N:8]=2)[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 85247Trimethylsilyl iodideHCID 21877088Acetonitrile methylene chlorideHCID 66731808HCID 66731808, compound

Product 1

HCID 24856097HCID 24856097, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a slightly cloudy mixture of dibenzyl 4-(2-(4-(4-(4-methylthiazol-2-yl)phthalazin-1-ylamino)phenoxy)pyridin-3-yl)pyrimidin-2-ylphosphoramidate (0.086 g, 0.11 mmol) in 3 mL 5:1 ACN/DCM was added iodotrimethylsilane (0.16 ml, 1.1 mmol) dropwise via syringe at ambient temperature under nitrogen. After 5 min, 0.6 mL MeOH was added and the stir bar was removed. The reaction was concentrated in vacuo and suspended in DCM and filtered. The resulting orange solid was collected and dried in vacuo to provide

Workup

  1. customthe stir bar was removed
  2. concentrationThe reaction was concentrated in vacuo
  3. filtrationfiltered
  4. customThe resulting orange solid was collected
  5. customdried in vacuo
  6. customto provide

Sources & evidence

ORD record
ord-08466897932744ef87ebaf30b52400f4
Source dataset
uspto-grants-2011_09
Patent number
US08022221B2

Reaction notes

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